Wyndham was an enthusiast of the British Empire, High Church Anglicanism, and government by a traditional aristocracy. From 1887, when he became the private secretary of Arthur James Balfour, he was a disciple of that future prime minister. Elected to the House of Commons in 1889, he spent much of the next nine years in writing for W.E. Henley’s weekly newspapers and in editing (1895–96) Sir Thomas North’s translation of Plutarch’s Lives and a volume (1898) of William Shakespeare’s poems.

After serving as undersecretary at the War Office (1898–1900), Wyndham, through Balfour’s influence, became chief secretary for Ireland (Nov. 7, 1900). His 1903 statute, by applying British government funds to Irish land transfers, made the sale of smallholdings and even whole estates profitable to landlords while guaranteeing purchase terms that peasant tenants could meet. Two years later (March 6, 1905) Wyndham resigned, either because of ill health or because the Conservatives thought that he approved a plan of Sir Antony (afterward Baron) MacDonnell, permanent undersecretary for Ireland, which called for a kind of Home Rule compromise called devolution—a limited central administration by Irishmen but without an Irish Parliament independent of Westminster.